Hydrochloric Acid → Verapamil

HRID 324915

Reaction equation

HRID 324915 reaction equation
[CH3:1][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:3].Cl.Cl>[2H]O[2H].CCOCC>[CH3:3][CH:2]([C:4]([C:24]1[CH:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=1)([C:22]#[N:23])[CH2:5][CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[CH3:9])[CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 62969Verapamil Hydrochloride

Product 1

HCID 2520Verapamil

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24602Deuterium OxideSolvent

Conditions

Temperature
90 °C

Procedure

Verapamil hydrochloride was added to a solution of 25% deuterated sulfuric acid in deuterated water (v/v) and deuterated methanol. The solution was stirred for 140 hours at 90° C. The pH was adjusted to 12.0 and the mixture extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, dried over magnesium sulfate and evaporated to yield a viscous oil. This oil was dissolved in ether and ethereal hydrochloride was added to precipitate the hydrochloride salt. The salt was collected by filtration and crystallized from ethyl acetate to obtain deuterated verapamil as a white solid.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto yield a viscous oil
  6. customto precipitate the hydrochloride salt
  7. filtrationThe salt was collected by filtration
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c5767c3ada7942e79ac52054414210be
Source dataset
uspto-grants-2001_04
Patent number
US06221335B1

Linked notes

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